About the PWHL
The Professional Women's Hockey League delivers world-class competition and fosters meaningful connections with fans and communities through operational excellence, purposeful partnerships, and a focus on long-term sustainability. We are dedicated to cultivating a workplace and league culture rooted in integrity, innovation, and inclusion — on and off the ice.
Position Summary
The PWHL is seeking a strategic Benefits Specialist to co-design and manage comprehensive benefits programs across our unique single-entity structure spanning the United States and Canada. This role offers the opportunity to leverage our employment model to create innovative, competitive benefits packages that differentiate the PWHL as an employer of choice for both staff and players. You'll partner closely with Finance, Legal, and external vendors to ensure compliant, cost-effective, high-touch benefits delivery while navigating cross-border complexities. This position is ideal for a benefits professional who thrives in a fast-paced, high-visibility environment and is passionate about advancing women's professional sports.
Key Duties & Responsibilities
- Co-design, implement, and administer strategic benefits programs (health, dental, vision, retirement, supplemental benefits) across US and Canadian operations
- Lead vendor management and ongoing relationship oversight for benefits providers
- Plan and execute annual open enrollment processes with comprehensive employee communications and support
- Administer all leave programs including FMLA, provincial leaves, parental leave, and disability benefits
- Ensure regulatory compliance with federal, state/provincial, and local benefits requirements in both countries
- Develop benefits education materials and deliver communication campaigns to maximize employee understanding
- Partner with Finance on benefits budgeting, forecasting, cost analysis, and reporting
- Conduct market research and benchmarking to maintain competitive benefits positioning
- Serve as the primary resource for employee benefits inquiries and issue resolution
Required Qualifications
- Bachelor's degree in Human Resources, Business Administration, or related field
- Minimum 5 years of progressive benefits administration experience, including multi-state and cross-border benefits management
- Strong knowledge of US benefits regulations (ERISA, ACA, COBRA, FMLA, etc.) and familiarity with Canadian provincial requirements
- Proficiency with ADP Workforce Now and benefits administration platforms
- Advanced Excel skills for data analysis and benefits modeling
- Demonstrated vendor management and contract negotiation experience
- Strong analytical skills with ability to interpret complex regulations and benefits data
- Excellent communication skills with ability to translate technical benefits concepts for diverse audiences
- Flexibility to work evenings and weekends during peak enrollment periods
Preferred Qualifications
- CEBS, CBP, or similar benefits certification
- Experience in professional sports, entertainment, or high-visibility industries
- Background implementing new benefits programs or system conversions
- Bilingual capabilities (English/French)
- Prior experience with single-entity or centralized employment models
Flexibility & Travel
Candidate must be able to work in a fully remote capacity with evenings and weekends during benefits enrollment periods and key events. Limited travel may be required for vendor meetings and team site visits.
The Professional Women's Hockey League is an equal opportunity employer, and all qualified applicants will receive consideration for employment without regard to race, color, religion, national origin, sex, sexual orientation, age, disability, gender identity, marital or veteran status, or any other protected class.
Background check will be conducted once a successful candidate is identified.
